HCID 66652223, compound → HCID 72309435, compound

Participants

Reaction Steps

Combine 6-Bromomethyl-4-(4-hydroxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-8-ol (0.037 g, 0.1 mmol), LiN3 (0.0213 g, 0.43 mmol), and DMF (1.5 ml) and heat at 90° C. for 3 hours. Cool, add ice and extract with ethyl acetate. Wash organic layer with 3× with water. Dry over anhydrous sodium sulfate and concentrate to a residue which yields after separation on silica gel with 20% EtOAC/hexanes, the titled compound (0.01 g, 34%). 1H NMR (CDCl3) 7.2 (d, J=8.4 Hz, 2H), 6.85 (d, J=8.4 Hz, 2H), 6.73 (s, 1H), 6.68 (s, 1H), 4.35 (s, 2H), 3.45 (m, 1H), 3.15 (m, 1H), 2.95 (m, 1H), 2.85 (m, 1H) 2.55 (m, 1H), 2.25 (m, 1H), 1.7-1.2 (m, 5H). MS m/z 334 (M−1).

Provenance & Evidence